Sodium Acetate → HCID 12488425, compound

HRID 647773Notes

Reaction equation

HRID 647773 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:25](=[O:26])[N:14]2[CH:15]([C:21]([O:23][CH3:24])=[O:22])[C:16]([CH3:20])(I)[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+]>C(#N)C>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:25](=[O:26])[N:14]2[C:15]([C:21]([O:23][CH3:24])=[O:22])=[C:16]([CH3:20])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 70361146HCID 70361146, compound

Product 1

HCID 12488425HCID 12488425, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 7-(2-phenoxyacetamido)-3-methyl-3-iodocepham-4-carboxylate (0.25 g.) in dry acetonitrile (10 cc) and sodium acetate (45 mg.) was heated under reflux for 4 hours and concentrated. The residue was mixed with water and extracted with chloroform. The chloroform layer was washed with an aqueous sodium thiosulfate solution and then with water, dried and concentrated. The residue was subjected to chromatography on silica gel and eluated with chloroform to yield crystals (50 mg.) of methyl 7-(2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylate, m.p. 124°-125° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated
  4. additionThe residue was mixed with water
  5. extractionextracted with chloroform
  6. washThe chloroform layer was washed with an aqueous sodium thiosulfate solution
  7. dry with materialwith water, dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0a21e8e798e14ea39e8fb6e437920231
Source dataset
uspto-grants-1983_10
Patent number
US04410458

Reaction notes

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